493-72-1Relevant articles and documents
Inhibition of Autophagy by a Small Molecule through Covalent Modification of the LC3 Protein
Chen, Kaixian,Chen, Zhifeng,Dang, Yongjun,Ding, Hong,Fan, Shijie,Hu, Junchi,Jiang, Hualiang,Li, Lianchun,Li, Quanfu,Lin, Tingting,Lu, Junyan,Luo, Cheng,Otomo, Chinatsu,Otomo, Takanori,Tan, Minjia,Tao, Hongru,Wan, Wei,Wen, Yi,Xie, Yuli,Xu, Pan,Yao, Zhiyi,Yue, Liyan,Zhang, Bidong,Zhang, Naixia,Zhang, Yuanyuan,Zhou, Bing,Zhu, Mingrui
supporting information, p. 26105 - 26114 (2021/11/09)
The autophagic ubiquitin-like protein LC3 functions through interactions with LC3-interaction regions (LIRs) of other autophagy proteins, including autophagy receptors, which stands out as a promising protein–protein interaction (PPI) target for the intervention of autophagy. Post-translational modifications like acetylation of Lys49 on the LIR-interacting surface could disrupt the interaction, offering an opportunity to design covalent small molecules interfering with the interface. Through screening covalent compounds, we discovered a small molecule modulator of LC3A/B that covalently modifies LC3A/B protein at Lys49. Activity-based protein profiling (ABPP) based evaluations reveal that a derivative molecule DC-LC3in-D5 exhibits a potent covalent reactivity and selectivity to LC3A/B in HeLa cells. DC-LC3in-D5 compromises LC3B lipidation in vitro and in HeLa cells, leading to deficiency in the formation of autophagic structures and autophagic substrate degradation. DC-LC3in-D5 could serve as a powerful tool for autophagy research as well as for therapeutic interventions.
Construction of Multiple-Substituted Chiral Cyclohexanes through Hydrogenative Desymmetrization of 2,2,5-Trisubstituted 1,3-Cyclohexanediones
Yu, Chang-Bin,Song, Bo,Chen, Mu-Wang,Shen, Hong-Qiang,Zhou, Yong-Gui
supporting information, p. 9401 - 9404 (2019/11/28)
The construction of chiral multiple-substituted cyclohexanes motifs is a challenging topic in organic synthesis. By the combination of desymmetrization and remote stereocontrol, a ruthenium-catalyzed transfer hydrogenative desymmetrization of 2,2,5-trisubstituted 1,3-cyclohexanediones has been successfully developed for the construction of chiral multiple-substituted cyclohexanes with high enantioselectivity and diastereoselectivity. When an ester group was introduced to the two-position, a hydrogenative desymmetrization/transesterification cascade occurred, affording the bicyclic lactones bearing three stereocenters, including two discrete stereocenters and one quaternary stereogenic center, with high enantioselectivity. The products are the multiple-substituted chiral cyclohexanes bearing the hydroxyl and carbonyl functional groups, which provide a new opportunity for further precise elaboration.
Dehydrogenative Formation of Resorcinol Derivatives Using Pd/C-Ethylene Catalytic System
El-Deeb, Ibrahim Yussif,Funakoshi, Tatsuya,Shimomoto, Yuya,Matsubara, Ryosuke,Hayashi, Masahiko
, p. 2630 - 2640 (2017/03/14)
The conversion of substituted 1,3-cyclohexanediones to the alkyl ethers of resorcinol using a Pd/C-ethylene system is reported. In these reactions, ethylene works as a hydrogen acceptor. The efficient synthesis of resveratrol was achieved using this protocol as a key step. In addition, the direct formation of substituted resorcinols was carried out by adding K2CO3 into the reaction media.
Iodine-Promoted Semmler–Wolff Reactions: Step-Economic Access to meta-Substituted Primary Anilines via Aromatization
Wang, Shi-Ke,You, Xia,Zhao, Da-Yuan,Mou, Neng-Jie,Luo, Qun-Li
supporting information, p. 11757 - 11760 (2017/09/07)
An atom- and step-economic access to an array of unprotected meta-substituted primary anilines was disclosed using the Semmler–Wolff reaction, promoted by molecular iodine. Therein, noble metal catalysts and inert atmosphere are unnecessary while the forcing reaction conditions and the lengthy synthesis can be avoided. The synthetic utility of this approach is evident in the de novo syntheses of three bioactive molecules with good total yields.
Synthesis of new 3-phenyl substituted dibenzo-1,4-diazepin-1-one derivatives
Wang, Fang-Ming,Bao, Dan,Wang, Ming,Li, Ming-Jun,Chen, Li-Zhuang,Han, Guang-Fan
, p. 664 - 667 (2015/02/18)
A new series of 3-phenyl substituted dibenzo-1,4-diazepin-1-one derivatives were synthesised by condensation of 5-phenylcyclohexane-1,3-dione, o-phenylenediamine and benzaldehydes. All the compounds were characterised by IR, MS, 1H NMR and elemental analysis. The crystal structure of 3-phenyl-11-(2-chlorophenyl)-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e] [1,4]diazepin-1-one was determined by X-ray single-crystal diffraction.
High-Yielding Total Synthesis of Sexually Deceptive Chiloglottones and Antimicrobial Dialkylresorcinols through an Organocatalytic Reductive Coupling Reaction
Madhavachary, Rudrakshula,Ramachary, Dhevalapally B.
supporting information, p. 7317 - 7323 (2016/02/20)
Biologically important, less-explored natural products of sexually deceptive chiloglottones, antimicrobial dialkylresorcinols, and their many analogues were synthesized in very good yields in a sequential two-pot manner by using an "organocatalytic reductive coupling reaction" as the key step. Sexually deceptive chiloglottones, antimicrobial dialkylresorcinols, and their many analogues are synthesized in very good yields in a sequential two-pot manner by using an "organocatalytic reductive coupling reaction" as the key step.
One-pot synthesis of fused pyrroles through a key gold-catalysis-triggered cascade
Zheng, Zhitong,Tu, Huangfei,Zhang, Liming
supporting information, p. 2445 - 2448 (2014/03/21)
A two-step, one-pot synthesis of fused pyrroles is realized by firstly condensing an N-alkynylhydroxammonium salt with a readily enolizable ketone under mild basic conditions and then subjecting the reaction mixture to a gold catalyst, which triggers a cascade reaction involving a facile initial [3.3]-sigmatropic rearrangement of the gold-catalysis product, that is, an N,O-dialkenylhydroxamine. The reaction provides a facile access to polycyclic pyrroles in moderate to good yields. A two-step, one-pot synthesis of fused pyrroles is realized by firstly condensing an N-alkynylhydroxammonium salt with a readily enolizable ketone under mild basic conditions and then subjecting the reaction mixture to a gold catalyst, which triggers a cascade reaction involving a facile initial [3.3]-sigmatropic rearrangement of the gold-catalysis product, that is, an N,O-dialkenylhydroxamine. The reaction provides a facile access to polycyclic pyrroles in moderate to good yields (see scheme). Copyright
Synthesis of 10-amino-9-aryl-2,3,4,5,6,7,9,10-octahydroacridine- 1,8-dione derivatives
Han, Guang-Fan,Cui, Bin,Chen, Li-Zhuang,Hu, Xiao-Lei
scheme or table, p. 195 - 199 (2012/04/17)
A series of novel 10-amino-9-aryl-2,3,4,5,6,7,9,10-octahydroacridine-1,8- dione derivatives 4 were synthesized by hydrazine or phenylhydrazine and 9-aryl-1,8-dioxo-2,3,4,5,6,7,9-heptahydroxanthene derivatives 3, which were prepared by 5-substituted-1,3-cyclohexanedione 1 and aromatic aldehydes 2 in the presence of concentrated H2SO4 as a catalyst in water. The structures of all compounds were characterized by IR, MS, 1H-NMR, and elemental analysis, and the title compounds possess good fluorescence properties..
Tandem reactions leading to benzo[c]chromen-6-ones and 3-substituted isocoumarins
Fan, Xuesen,He, Yan,Cui, Liangyan,Guo, Shenghai,Wang, Jianji,Zhang, Xinying
supporting information; experimental part, p. 673 - 677 (2012/03/10)
A simple and convenient protocol for the synthesis of benzo[c]chromen-6- ones and 3-substituted isocoumarins through a CuI-catalyzed tandem reaction of 2-bromobenzoates withcyclohexane-1,3-diones or acyclic 1,3-diones is developed. This strategy can also be extended to the one-pot synthesis of isoquinolin-1(2H)-one and 3,4-dihydrophenanthridine-1,6(2H,5H)-dione. A simple and convenient protocol for the synthesis of benzo[c]chromen-6-ones and 3-substituted isocoumarins through a CuI-catalyzed tandem reaction of 2-bromobenzoates with cyclohexane-1,3-dione or acyclic 1,3-dione has been developed. This strategy can also be extended to the one-pot synthesis of isoquionlin-1(2H)-one and 3,4-dihydrophenanthridine-1,6-(2H,5H)-dione. Copyright
Synthesis and crystal structure of 4,7-diaryl-5-oxo-4H-benzo[b]pyran derivatives
Cui, Bin,Chen, Li-Zhuang,Hu, Xiao-Lei,Wang, Ming,Han, Guang-Fan
, p. 900 - 904 (2012/10/29)
A green and convenient approach to the synthesis of a series of 4,7-diaryl-5-oxo-4H-benzo[b]pyran derivatives from appropriate aromatic aldehydes and 5-aryl-1,3-cyclohexanedione with malononitrile in the presence of dilute HCl as catalyst (30 mmol/L) is described. This method provides several advantages such as environmental friendliness, low cost, high yields, and simple work up procedure. The structures of all compounds were characterized by infrared (IR), mass spectrometry (MS), 1H NMR, and elemental analysis. The crystal structure of trans/cis-2-amino-3-cyano-7-(4'-methoxo- phenyl)-4-phenyl-5-oxo-4H-benzo[b]pyran, g, was determined by single crystal X-ray diffraction analysis. The crystal of compound g belongs to monoclinic with space group P 21/c, a = 8.477(3) nm, b = 18.948(6) nm, c = 24.915(7) nm, α = 90.00°, β = 107.388(11)°, γ= 90.00°, Z = 8, V = 3.819(2) nm3, R1 = 0.0754, wR2 = 0.2042.
